FR3013351A1 - PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND - Google Patents

PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND Download PDF

Info

Publication number
FR3013351A1
FR3013351A1 FR1361169A FR1361169A FR3013351A1 FR 3013351 A1 FR3013351 A1 FR 3013351A1 FR 1361169 A FR1361169 A FR 1361169A FR 1361169 A FR1361169 A FR 1361169A FR 3013351 A1 FR3013351 A1 FR 3013351A1
Authority
FR
France
Prior art keywords
preparation
aromatic compound
aromatic
condensation reaction
reaction
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Granted
Application number
FR1361169A
Other languages
French (fr)
Other versions
FR3013351B1 (en
Inventor
Laurent Garel
Flavie Sarrazin
Olivier Back
Kevin Olivon
Mathieu Pucheault
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Rhodia Operations SAS
Original Assignee
Rhodia Operations SAS
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority to FR1361169A priority Critical patent/FR3013351B1/en
Application filed by Rhodia Operations SAS filed Critical Rhodia Operations SAS
Priority to RU2016123378A priority patent/RU2712754C2/en
Priority to PCT/EP2014/074658 priority patent/WO2015071431A1/en
Priority to US15/036,871 priority patent/US10544081B2/en
Priority to CN201480073309.1A priority patent/CN105916834A/en
Priority to JP2016530828A priority patent/JP6635921B2/en
Priority to EP14799417.2A priority patent/EP3068755A1/en
Publication of FR3013351A1 publication Critical patent/FR3013351A1/en
Application granted granted Critical
Publication of FR3013351B1 publication Critical patent/FR3013351B1/en
Expired - Fee Related legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C45/00—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds
    • C07C45/27—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation
    • C07C45/32—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen
    • C07C45/37—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups
    • C07C45/39—Preparation of compounds having >C = O groups bound only to carbon or hydrogen atoms; Preparation of chelates of such compounds by oxidation with molecular oxygen of >C—O—functional groups to >C=O groups being a secondary hydroxyl group
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C47/00—Compounds having —CHO groups
    • C07C47/52—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings
    • C07C47/575—Compounds having —CHO groups bound to carbon atoms of six—membered aromatic rings containing ether groups, groups, groups, or groups
    • C07C47/58—Vanillin
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
    • C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
    • C07C51/367—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by introduction of functional groups containing oxygen only in singly bound form
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/582—Recycling of unreacted starting or intermediate materials

Abstract

On décrit un procédé de préparation de composé(s) aromatique(s) portant au moins un groupement mandélique -CHOH-COOH comprenant une réaction de condensation d'au moins un composé aromatique avec l'acide glyoxylique ou ses dérivés, ladite réaction de condensation étant mise en œuvre substantiellement en l'absence de tout acide ou toute base ajouté(e) au milieu réactionnel. La réaction de condensation est suivie d'une réaction d'oxydation pour l'obtention d'aldéhyde aromatique.There is described a process for the preparation of aromatic compound (s) carrying at least one mandelic group -CHOH-COOH comprising a condensation reaction of at least one aromatic compound with glyoxylic acid or its derivatives, said condensation reaction being implemented substantially in the absence of any acid or base added to the reaction medium. The condensation reaction is followed by an oxidation reaction to obtain aromatic aldehyde.

Description

La présente invention su idppurte au domaine de la préparation de composés aromatiques mandéliques et de composés aldéhydes aromatiques obtenus à partir desdits composés aromatiques mandéliques De manière plus particulière, a présente invention se rapporte à la préparation de composés aromatiques hydroxymandéliques préparation c mposés aldéh )xyaro 4-hydi nci( jd n iration À' nadir es natIlmilP telle nue 2( 1 jeu 4,11 ebIllt linse e oeuvre de la réact condensation aveu ull gaïac nécessite une pe de recyc e de ce réactif. La présente invention a pou n procédé de préparation de composé aromatique(s) mandéli )mposé(s) aldéhyde 15 20 avantac inmi I s-1 thylinuui uenzofurall sunt péfel ès. Parmi les composés cilL iues ,lycycliques, le naphtol est préféré. Les benzènes substitues sont préférentiellement des benzènes substitués par un ou plusieurs groupes choisis rmi un groupe . yle, alcényle, alkoxy, hydroxyalky e, xyalkyle, cycloalkyle, yle. arylalky e, un upe hydroxyle, un grau d'halogène, un lier EflZ 3-trim ét hoxy 10 A rkOflC vicinaux pcUVel.t ces sur d__ es de c-isemble ivec les atomes 'u carboric. rten ycle saww, insaturé ou aromatique ayant de et con r-Ituellement I ou plusieurs hétéroatome. Dans ladite formul position i du groupe hydre préférentiellement lib ire del .ibstituant.The present invention is relevant to the field of the preparation of mandelic aromatic compounds and aromatic aldehyde compounds obtained from said mandelic aromatic compounds. More particularly, the present invention relates to the preparation of aromatic hydroxymandelic compounds prepared in the presence of aldehydes. As a result of the above-mentioned condensation reaction, the reaction of this reagent must be carried out with the aid of a recyc e method. Preparation of aromatic compound (s) mandeli) compound (s) aldehyde 15 pre-acetyl-1-thylinuulfuenzofurall sunt pefel Amongst the cyclic, lycyclic compounds, naphthol is preferred.The substituted benzenes are preferentially benzenes substituted by one or more groups selected from: yl, alkenyl, alkoxy, hydroxyalkyl, xylalkyl, cycloalkyl, yl, aryl; Here, a hydroxylated hydroxylate, a halogen salt, a 3-trimethyloxyalkylate, and a trifluorinated alkali metal can be used in conjunction with carboric carbon atoms. unsaturated or aromatic radical having at least one or more heteroatoms. In said formula i position of the hydra group is preferably free of the substituent.

Dans én^ ellx alk ne, Dans u Jeux aLol I ICb ' 'ne ma 3nt es enl K p upe alKyiène. a "nylenE fon 10 20 30 àthylphénol 2-propylphénol 2-sec-butylphénol ert-butylphénol ert-butylphénol néthoxyphél )roi -litrophén. ényl nol mi;rrn JIJI I nule (I' lent d- penzeniques : ph( 131 ICUIJ Ilielange.Le 91yoxylaLe alement avantageusement employés comme ligands oxygénés. procédé de préparation Fi ntion, la réaction de condensation et de base autr 10 ns pn 25 35 Il (-di 4+1 y e y 1L4 Ç entre 0.1 ei Us préféremiellen-ient enue et t de manière encore plus préférée il est voisin de 1 (c'est-à-dire compris en 0.9 et 1,1) de sorte que le ratio équimolaire entre ledit composé aromatiquE et l'acide glyoxyli^ ou ses dérivés é le recyclage de un ou l'autre desdits 10 15 lent entre n 20 n 25 f re éth uct, troisierne nsatlo e glyoxylique avec I e gaiacol et le guÉ - à la co-pr idroxyma substitué en orthi oupe hydrc léthox es aryiacetiqu s préférenticement lroxya tiques ary o cétiqu r c 1C 11e, bau anèse, rer, eI et osmium. rrere neilement, on choisit ies oenves nadium E et de manière préfÉ :atalys en-iploy( en d'ar 10 15 ati Là I I Il ICI z .on d'oxydation, on procède avantageusement une extraction d s d aldéhyde (s) aromatique(s) à l'aide d'un solvant organique Ledit solvant organique solubilise le(s)dit(s) aldéhyde nrnm (11.1PiQ rianc nilieu aqueux. On fait avantageusement appe organ lui soit tiqL méthane, Drober rime iIrrnIs nrnnAnnl l'icnnropan 5 mme mv A mélange alL,Lnm u_icH cnemple me lano - cristallisation sous vide sorage en discontinu ; chage du(es)dit(s) aldéhyde(s) aromati, ne température d a u à la terril fusion du - dernm nt nt et d'au r )st en tnute b ctionr 35 I 4 I mise e iadiie (eal I LI tJAyUcl1ll_11 I t Ici val iduote niui ii (NH4V03) c- oxyde de vanadium V Les conditions opératoires pour la mise ( dite réactjor sont notamment celles .-,rit( Jans la demande c. )revet VVO 2008/148760 ix ( iani 2C pement mandelioue par une réaction de ^ ndenu_.. q yoxylique sur un composé aromatique. Dans un réacteur de 5C i d'unE )ride de température et du agitation mécanique, on ntrc t ual é d'un composé aromatique lequel est uffe à la terni fug e ta températl IE )Ieau réac der ice, I ont 10In Alkaline, In a Games, Iol, I, and I are not in the Kyle. Example 2-propylphenol 2-sec-butylphenol-4-butylphenol-2-propylphenol-2-sec-butylphenol-4-butylphenol-4-butylphenol-4-nitrophenol-4-nitrophenol-2-propylphenol-2-propylphenol-2-propylphenol. The alkoxylates are advantageously employed as oxygenated ligands in the process of preparation, the condensation and base reaction being carried out between 0.1 and 0.15 μl. even more preferably it is close to 1 (i.e., included in 0.9 and 1.1) so that the equimolar ratio between said aromatic compound and glyoxyli acid or its derivatives and the recycling of one or Another of said compounds is between ethylene, ethyl and glyoxyl, and is substituted with ortho- or hydrophilic ethoxides and is preferably substituted with arylacetic acid. 1C 11e, bau anèse, rer, eI and osmium. For example, in the case of oxidation it is advantageous to carry out extraction of the aromatic aldehyde (s) using An organic solvent solubilizes said (s) aldehyde nrnm (11.1PiQ rianc aqueous medium. It is advantageously referred to it as either methane or methanol, the same polymer or mixture being mixed in the same way as in the case of discontinuous lano-crystallization under vacuum; display of the said aromatic aldehyde (s), the temperature at the end of the melting furnace of the last and of the last hour of the production of the product. The operating conditions for the setting of said reactant are, in particular, those of the present invention (see application V), and VVO 2008/148760 ix (iani 2C mandelioue). by a reaction of yoxylic content on an aromatic compound, in a reactor of 5 ° C. a temperature wrinkle and mechanical stirring, an aromatic compound is used, which is removed at the end of its life. e the temperature of the water, I have 10

Claims (19)

REVENDICATIONS1. Procédé de préparation de composé(s) aromatique(s) portant au moins un groupement mandélique -CHOH-COOH comprenant une réaction de condensation d'au moins un composé aromatique avec l'acide glyoxylique ou ses dérivés, ladite réaction de condensation étant mise en oeuvre substantiellement en l'absence de tout acide ou toute base ajouté(e) au milieu réactionnel.REVENDICATIONS1. Process for the preparation of aromatic compound (s) carrying at least one mandelic group -CHOH-COOH comprising a condensation reaction of at least one aromatic compound with glyoxylic acid or its derivatives, said condensation reaction being carried out substantially in the absence of any acid or base added to the reaction medium. 2. Procédé de préparation de composé(s) aromatique(s) selon la revendication 1 dans lequel ledit composé aromatique employé en tant que réactif dans la réction de condensation est choisi parmi les benzènes substitués, le phénol et les phénols substitués, les composés aromatiques hétérocycliques, les 15 composés aromatiques polycycliques.A process for the preparation of aromatic compound (s) according to claim 1, wherein said aromatic compound employed as a reagent in the condensation rection is selected from substituted benzenes, phenol and substituted phenols, aromatic compounds. heterocyclic, polycyclic aromatic compounds. 3. Procédé de préparation de composé(s) aromatique(s) selon la revendication 2 dans lequel lesdits phénols substitués répondent à la formule suivante (I) : OH 20 (I) dans ladite formule, - R représente un ou plusieurs substituants, identiques ou différents, - x, nombre de substituants sur un cycle, est un nombre entier compris entre 1 et 4, 25 - lorsque x est supérieur à 1, deux groupes R placés sur deux atomes de carbone vicinaux peuvent former ensemble et avec les atomes de carbone qui les portent un cycle saturé, insaturé ou aromatique, ayant de 5 à 7 atomes et comprenant éventuellement un ou plusieurs hétéroatomes. 303. Process for the preparation of aromatic compound (s) according to claim 2, in which the said substituted phenols correspond to the following formula (I): ## STR3 ## in which formula R represents one or more substituents, which are identical. or different, - x, number of substituents on a ring, is an integer between 1 and 4, - when x is greater than 1, two R groups placed on two vicinal carbon atoms can together form and with the atoms of carbon which carries them a saturated, unsaturated or aromatic ring, having from 5 to 7 atoms and optionally comprising one or more heteroatoms. 30 4. Procédé de préparation de composé(s) aromatique(s) selon la revendication 3 dans lequel la position en para du groupe hydroxyle est non substituée. 3 0 1 3 3 5 1 194. Process for the preparation of aromatic compound (s) according to claim 3 wherein the para position of the hydroxyl group is unsubstituted. 3 0 1 3 3 5 1 19 5. Procédé de préparation de composé(s) aromatique(s) selon la revendication 3 ou la revendication 4 dans lequel les phénols substitués sont : l'o-crésol, le m-crésol, le 3-éthylphénol, le 2-tert-butylphénol, le gaïacol, le guétol. 5A process for the preparation of aromatic compound (s) according to claim 3 or claim 4 wherein the substituted phenols are: o-cresol, m-cresol, 3-ethylphenol, 2-tert- butylphenol, guaiacol, guetol. 5 6. Procédé de préparation de composé(s) aromatique(s) selon l'une des revendications 1 à 5 dans lequel l'acide glyoxylique est utilisé sous forme monohydrate (CHO-CO2H, H20).6. Process for the preparation of aromatic compound (s) according to one of claims 1 to 5 wherein the glyoxylic acid is used in monohydrate form (CHO-CO2H, H20). 7. Procédé de préparation de composé(s) aromatique(s) selon l'une des 10 revendications 1 à 6 dans lequel ladite réaction de condensation est mise en oeuvre en présence d'au moins un catalyseur ajouté audit milieu réactionnel en quantité catalytique.7. Process for the preparation of aromatic compound (s) according to one of claims 1 to 6 wherein said condensation reaction is carried out in the presence of at least one catalyst added to said reaction medium in a catalytic amount. 8. Procédé de préparation de composé(s) aromatique(s) selon la revendication 15 7 dans lequel ledit catalyseur est un catalyseur à base de métaux de transition choisi parmi les complexes de métaux de transition comportant des ligands oxygénés.8. Process for the preparation of aromatic compound (s) according to claim 7 wherein said catalyst is a transition metal catalyst selected from transition metal complexes having oxygenated ligands. 9. Procédé de préparation de composé(s) aromatique(s) selon la revendication 20 7 ou la revendication 8 dans lequel ledit catalyseur est choisi parmi l'acétate de fer(II) (Fe(0Ac)2) et l'acétate de fer (III) (Fe(0Ac)3), l'acétate de cuivre (II) (Cu(OAc)2), l'acétylacétonate de fer (II) (Fe(acac)2) et l'acétylacétonate de fer (III) (Fe(acac)3), l'acétylacétonate de cuivre (II) (Cu(acac)2) et l'acétylacétonate de cuivre (III) (Cu(acac)3). 25A process for preparing an aromatic compound (s) according to claim 7 or claim 8 wherein said catalyst is selected from iron (II) acetate (Fe (OAc) 2) and iron (III) (Fe (OAc) 3), copper (II) acetate (Cu (OAc) 2), iron (II) acetylacetonate (Fe (acac) 2) and iron acetylacetonate ( III) (Fe (acac) 3), copper (II) acetylacetonate (Cu (acac) 2) and copper (III) acetylacetonate (Cu (acac) 3). 25 10. Procédé de préparation de composé(s) aromatique(s) selon l'une des revendications 1 à 9 dans lequel ladite réaction de condensation est mise en oeuvre en présence d'un solvant choisi parmi l'eau, un hydrocarbure aromatique, un alcool, un mélange eau-alcool. 3010. Process for the preparation of aromatic compound (s) according to one of claims 1 to 9 wherein said condensation reaction is carried out in the presence of a solvent selected from water, an aromatic hydrocarbon, a alcohol, a water-alcohol mixture. 30 11. Procédé de préparation de composé(s) aromatique(s) selon l'une des revendications 1 à 9 dans lequel ladite réaction de condensation est mise en oeuvre en l'absence d'un solvant. 3511. Process for the preparation of aromatic compound (s) according to one of claims 1 to 9 wherein said condensation reaction is carried out in the absence of a solvent. 35 12. Procédé de préparation de composé(s) aromatique(s) selon l'une des revendications 1 à 11 dans lequel le rapport molaire entre le composé aromatique et l'acide glyoxylique ou ses dérivés est voisin de 1. 301 3 3 5 1 2012. Process for the preparation of aromatic compound (s) according to one of claims 1 to 11 wherein the molar ratio between the aromatic compound and the glyoxylic acid or its derivatives is close to 1. 301 3 3 5 1 20 13. Procédé de préparation de composé(s) aromatique(s) selon l'une des revendications 1 à 12 tel qu'il consiste à mettre en oeuvre la réaction de condensation de l'acide glyoxylique avec le gaïacol ou la réaction de condensation de l'acide glyoxylique avec le guétol ou encore la réaction de 5 condensation de l'acide glyoxylique avec le gaïacol et le guétol.13. Process for the preparation of aromatic compound (s) according to one of claims 1 to 12 as it consists in carrying out the condensation reaction of glyoxylic acid with guaiacol or the condensation reaction of glyoxylic acid with guetol or the condensation reaction of glyoxylic acid with guaiacol and guetol. 14. Procédé de préparation d'aldéhyde(s) aromatique(s) comprenant la réaction de condensation mise en oeuvre selon le procédé de l'une des revendications 1 à 13 suivie d'une réaction d'oxydation du(es)dit(s) composé(s) aromatique(s) 10 portant au moins un groupement mandélique -CHOH-COOH.14. Process for the preparation of aromatic aldehyde (s) comprising the condensation reaction carried out according to the process of one of Claims 1 to 13 followed by an oxidation reaction of the said (s) ) aromatic compound (s) carrying at least one mandelic group -CHOH-COOH. 15. Procédé de préparation d'aldéhyde(s) aromatique(s) selon la revendication 14 dans lequel ladite réaction d'oxydation est mise en oeuvre sans ajout d'agent alcalin.15. Process for the preparation of aromatic aldehyde (s) according to claim 14 wherein said oxidation reaction is carried out without the addition of alkaline agent. 16. Procédé de préparation d'aldéhyde(s) aromatique(s) selon la revendication 14 ou la revendication 15 dans lequel ladite réaction d'oxydation est mise en oeuvre en présence d'eau en tant que solvant.16. Process for the preparation of aromatic aldehyde (s) according to claim 14 or claim 15 wherein said oxidation reaction is carried out in the presence of water as a solvent. 17. Procédé de préparation d'aldéhyde(s) aromatique(s) selon l'une des revendications 14 à 16 dans lequel ladite réaction d'oxydation est conduite en présence d'un catalyseur choisi parmi les dérivés du chrome, cobalt, cuivre, vanadium, manganèse, fer, nickel et osmium.17. Process for the preparation of aldehyde (s) aromatic (s) according to one of claims 14 to 16 wherein said oxidation reaction is conducted in the presence of a catalyst selected from the derivatives of chromium, cobalt, copper, vanadium, manganese, iron, nickel and osmium. 18. Procédé de préparation d'aldéhyde(s) aromatique(s) selon l'une des revendications 14 à 17 tel qu'il consiste à préparer de la vanilline et/ou de l'éthylvanilline.18. Process for the preparation of aromatic aldehyde (s) according to one of claims 14 to 17 such that it consists in preparing vanillin and / or ethyl vanillin. 19. Procédé de préparation d'aldéhyde(s) aromatique(s) selon l'une quelconque des revendications 14 à 18, ladite réaction d'oxydation étant conduite en présence d'au moins un agent oxydant et d'au moins un catalyseur et substantiellement en l'absence de tout acide ou toute base ajouté(e) au milieu réactionnel soumis à ladite réaction d'oxydation.3519. Process for the preparation of aromatic aldehyde (s) according to any one of claims 14 to 18, said oxidation reaction being conducted in the presence of at least one oxidizing agent and at least one catalyst and substantially in the absence of any acid or base added to the reaction medium subjected to said oxidation reaction.
FR1361169A 2013-11-15 2013-11-15 PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND Expired - Fee Related FR3013351B1 (en)

Priority Applications (7)

Application Number Priority Date Filing Date Title
FR1361169A FR3013351B1 (en) 2013-11-15 2013-11-15 PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND
PCT/EP2014/074658 WO2015071431A1 (en) 2013-11-15 2014-11-14 Process for preparing mandelic aromatic compounds and aromatic aldehyde compounds
US15/036,871 US10544081B2 (en) 2013-11-15 2014-11-14 Process for preparing mandelic aromatic compounds and aromatic aldehyde compounds
CN201480073309.1A CN105916834A (en) 2013-11-15 2014-11-14 Process for preparing mandelic aromatic compounds and aromatic aldehyde compounds
RU2016123378A RU2712754C2 (en) 2013-11-15 2014-11-14 Method of producing almond aromatic compounds and aromatic aldehyde compounds
JP2016530828A JP6635921B2 (en) 2013-11-15 2014-11-14 Production method of mandelic acid aromatic compound and aromatic aldehyde compound
EP14799417.2A EP3068755A1 (en) 2013-11-15 2014-11-14 Process for preparing mandelic aromatic compounds and aromatic aldehyde compounds

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
FR1361169A FR3013351B1 (en) 2013-11-15 2013-11-15 PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND

Publications (2)

Publication Number Publication Date
FR3013351A1 true FR3013351A1 (en) 2015-05-22
FR3013351B1 FR3013351B1 (en) 2016-01-01

Family

ID=50137802

Family Applications (1)

Application Number Title Priority Date Filing Date
FR1361169A Expired - Fee Related FR3013351B1 (en) 2013-11-15 2013-11-15 PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND

Country Status (7)

Country Link
US (1) US10544081B2 (en)
EP (1) EP3068755A1 (en)
JP (1) JP6635921B2 (en)
CN (1) CN105916834A (en)
FR (1) FR3013351B1 (en)
RU (1) RU2712754C2 (en)
WO (1) WO2015071431A1 (en)

Families Citing this family (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20190031588A1 (en) 2017-07-28 2019-01-31 Rhodia Operations New vanillin and or ethylvanillin, process for their preparations and use thereof
CN111359662B (en) * 2018-12-26 2023-01-13 万华化学集团股份有限公司 Copper ligand catalyst, preparation method thereof and application thereof in mandelic acid oxidation reaction
CN111848377B (en) * 2020-08-18 2022-12-06 重庆化工职业学院 Preparation method of ethyl vanillin
FR3116819B1 (en) 2020-12-01 2023-11-17 Rhodia Operations Process for preparing frambinone
CN113121323B (en) * 2021-03-19 2022-12-16 上海应用技术大学 Preparation method of p-hydroxybenzaldehyde
CN114082449B (en) * 2021-12-01 2023-10-17 万华化学集团股份有限公司 Preparation method and application of aluminum ligand catalyst

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2640083A (en) * 1949-11-09 1953-05-26 Olin Mathieson Manufacture of vanillin and its homologues
EP0368696A1 (en) * 1988-11-08 1990-05-16 Societe Francaise Hoechst Process for the industrial manufacture of sodium parahydroxymandelate
EP0987245A1 (en) * 1998-09-15 2000-03-22 Gerard Kessels S.A. A method of preparing 2- and 4-hydroxymandelic acid

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
SU55779A1 (en) * 1938-11-07 1938-11-30 М.А. Яхилевич The method of obtaining vanilla
US4163759A (en) * 1971-03-31 1979-08-07 Haarmann & Reimer Gesellschaft Mit Beschrankter Haftung Process for preparing aromatic hydroxyaldehydes
US4048236A (en) * 1975-03-07 1977-09-13 Ube Industries, Ltd. Process for preparing o-alkoxy-p-allylphenols
DE2754490A1 (en) 1977-12-07 1979-06-13 Haarmann & Reimer Gmbh PROCESS FOR THE PREPARATION OF 3,4-METHYLENIOXYMANDEL ACID
JPS5620538A (en) 1979-07-27 1981-02-26 Brichima Manufacture of aromatic hydroxy and alkoxyaldehyde
JPS5998033A (en) 1982-11-26 1984-06-06 Nippon Synthetic Chem Ind Co Ltd:The Preparation of mandelic acid
FR2693458B1 (en) * 1992-07-10 1994-12-09 Rhone Poulenc Chimie Process for para-hydroxyalkylation of hydroxylated aromatic compounds.
US6664380B1 (en) 1999-08-18 2003-12-16 The Institute Of Applied Catalysis Perfluorosulfonylmethide compounds; use thereof for carbon-carbon bond formation
JP2004269451A (en) 2003-03-11 2004-09-30 Taoka Chem Co Ltd Method for producing mandelic acid derivative
FR2917085B1 (en) 2007-06-06 2009-07-17 Rhodia Recherches & Tech PROCESS FOR THE PREPARATION OF HYDROXYAROMATIC ALDEHYDE
FR2933974B1 (en) 2008-07-18 2010-09-17 Rhodia Operations PROCESS FOR SEPARATING AROMATIC ALDEHYDE
JP6081797B2 (en) * 2009-07-07 2017-02-15 バイエル・インテレクチュアル・プロパティ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツングＢａｙｅｒ Ｉｎｔｅｌｌｅｃｔｕａｌ Ｐｒｏｐｅｒｔｙ ＧｍｂＨ Process for the preparation of (2,4-dimethylbiphenyl-3-yl) acetic acid, their esters and intermediates

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2640083A (en) * 1949-11-09 1953-05-26 Olin Mathieson Manufacture of vanillin and its homologues
EP0368696A1 (en) * 1988-11-08 1990-05-16 Societe Francaise Hoechst Process for the industrial manufacture of sodium parahydroxymandelate
EP0987245A1 (en) * 1998-09-15 2000-03-22 Gerard Kessels S.A. A method of preparing 2- and 4-hydroxymandelic acid

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
NIU DONG-FANG ET AL: "Improved synthesis of 3-methoxy-4-hydroxymandelic acid by glyoxalic acid method", TETRAHEDRON, vol. 69, no. 38, 23 September 2013 (2013-09-23), pages 8174 - 8177, XP028688564, ISSN: 0040-4020, DOI: 10.1016/J.TET.2013.07.031 *

Also Published As

Publication number Publication date
JP6635921B2 (en) 2020-01-29
US10544081B2 (en) 2020-01-28
JP2016538285A (en) 2016-12-08
US20160297735A1 (en) 2016-10-13
FR3013351B1 (en) 2016-01-01
RU2712754C2 (en) 2020-01-31
CN105916834A (en) 2016-08-31
EP3068755A1 (en) 2016-09-21
WO2015071431A1 (en) 2015-05-21
RU2016123378A (en) 2017-12-18

Similar Documents

Publication Publication Date Title
FR3013351A1 (en) PROCESS FOR THE PREPARATION OF MANDELIC AROMATIC COMPOUND AND AROMATIC ALDEHYDE COMPOUND
Ni et al. Functionalized chiral ionic liquid as recyclable organocatalyst for asymmetric Michael addition to nitrostyrenes
Ma et al. D-Xylonic acid: a solvent and an effective biocatalyst for a three-component reaction
WO2008148760A2 (en) Process for preparing a hydroxyaromatic aldehyde
Nguyen et al. Synthesis of polyhydroquinolines and propargylamines through one-pot multicomponent reactions using an acidic ionic liquid immobilized onto magnetic Fe 3 O 4 as an efficient heterogeneous catalyst under solvent-free sonication
CA1077061A (en) Process for the oxydation of .beta.-ethilenic ketones
JPH06306078A (en) New synthesis route of mesotetrahydrocarbyl- or substituted hydrocarbylporphyrin compound and its derivative
Wang et al. One‐Pot Synthesis of cis‐Isoquinolonic Acid Derivatives via Three‐Component Reaction of Homophthalic Anhydride with Aldehydes and Amines using Ytterbium (III) Triflate as Catalyst
EP2651866B1 (en) Process for preparing a polyol ether
Dai et al. Enantioselective oxidation of sulfides with H 2 O 2 catalyzed by a pre-formed manganese complex
Arian et al. Novel sultone based Brønsted acidic ionic liquids with perchlorate counter-anion for one-pot synthesis of 2H‑indazolo [2, 1‑b] phthalazine‑triones
EP0877726B1 (en) Aromatic compound acylation method
KR101707237B1 (en) Process for preparing substituted 1,4-quinone methides
US20180258115A1 (en) Brønsted-acidic fluoroalkyl phosphonates
CN114057558B (en) Synthesis method, catalytic system and application of 3, 5-trimethylhexanal
EP0200657B1 (en) Process for the preparation of trifluoroethoxy- or trifluoroethylthiobenzenes
EP0432006B1 (en) Process for hydroxylating phenols and phenol ethers
CA1312625C (en) Process for the preparation of aromatic aldehydes
EP0324692B1 (en) Process for the preparation of hydroxyalkylating agents, the agents as prepared and their use
EP0299893A2 (en) Process for hydroxylating phenols and phenol ethers
EP0077279A1 (en) Process for the preparation of orthohydroxybenzaldehydes
EP0437586B1 (en) Substituted phenyl meso-tetraphenyl porphyrins
Carreño et al. Direct Synthesis of N‐Arylquinone Imine Acetals and Quinol Imines from Acetals
EP0408418B1 (en) Method of hydroxylating phenols and phenol ethers
WO2016102785A1 (en) Novel polymers containing metal sulfonate functions, methods for the production thereof and uses of same as catalysts

Legal Events

Date Code Title Description
PLFP Fee payment

Year of fee payment: 3

PLFP Fee payment

Year of fee payment: 4

PLFP Fee payment

Year of fee payment: 5

PLFP Fee payment

Year of fee payment: 6

PLFP Fee payment

Year of fee payment: 7

ST Notification of lapse

Effective date: 20210705